Author's Note: This story has been on my mind for weeks before I finally got it out. I really hope you enjoy reading it as much as I enjoyed writing it (please drop me a review if you have any constructive criticism or other comments).

Disclaimer: I do not own Supernatural or any of the characters from the show. The plot, however, is wholly mine (together with my OC).

Chapter 1: Of Dangerous Deliveries and Dilemmas

She could feel the grief and pain of Ethan Miller even before she entered the house. Elise was right – her husband was self-destructing without her. Anessa glanced down at Elise's letter, then at the overflowing mailbox. Ethan was definitely not going
to read anything in it for the foreseeable future. So simply leaving the letter in there was off the table. With a sigh, she flew into the house – reappearing to the human eye in the master bedroom shared by Ethan and Elise.

It was littered with memories, either captured in photographs or video, Ethan thrashing at the heart of the mess in the throes of a vicious nightmare on Elise's side of the bed. She was by his side before he could spring awake, sending him into a dreamless
sleep with her grace. The moment his breathing evened out, she was on her feet again, deft fingers releasing Elise's diary from its prison beneath the false bottom of her drawer. This she slipped into Ethan's limp hand, the letter tucked safely inside.
She took her leave quickly, praying that her errand remained undiscovered.

Thankfully, Josiah barely looked her way when she passed him. Air left her lungs in a long hiss once she was sure he was out of earshot. Her absence had failed to arouse any suspicion. For now, she did not need to fear the possibility of being strapped
to Heaven's torture-table. With a skip in her step, she ducked into the Winchesters' Heaven. She had a promise to keep, after all.

Mary Winchester's smile greeted her on her way to the dining area, obviously pleased that she had decided to show up. On the other hand, her husband did not bother to acknowledge her presence when she slid into the seat besidehis. John Winchester
was an intimidating man, even with his nose buried in a newspaper. She glued her eyes to the tablecloth, trying to ignore his blatant animosity towards her. After all, her brothers did send his sons to hell and back. Literally.

'How was Earth?'

The question jolted her out of her thoughts. 'What?' She answered lamely, slowly lifting her head.

'Ellen told me you were headed down there,' he continued calmly, folding his newspaper.

'Loud,' she replied distractedly, still unable to believe that he was actually talking to her.

John captured her gaze with his. 'How's Ethan Miller holding up? Heard his wife just passed.'

She tensed, icy fear trickling over her. He couldn't possibly know.

'Not well,' she answered carefully, 'H-He's devastated.'

'Bet you that letter you gave him would cheer him right up.'

She ripped her gaze away from his, right hand capturing her left in a white-knuckled grip, 'I don't know what you're talking about.'

'Don't play dumb with me, kid,' John looked like the cat that ate the canary, flashing her a dimpled smile. 'I know exactly what you did.'

All colour drained from her face as she scrambled to her feet. This was a trap and, like a fool, she had walked right into it. She had minutes, maybe seconds, before Josiah and the others came storming in. She turned to leave, only for a strong hand to
clamp tightly around her wrist. She whirled around, her blue eyes clashing with the intense browns of John Winchester.

'Sit down, 'he commanded, his tone leaving no room for argument. 'I'm not going to turn you in.'

She searched his face for a full minute for any form of deception. Finding none, she did as she was told, eyeing him warily. The Winchesters were not known for their unconditional mercy.

'Listen carefully, sweetheart,' John spoke gently but firmly, 'I don't trust your kind as far as I can throw 'em but I need to get a message to my boys while it's still quiet. '

She pressed her lips into a thin line, the agonizing fear of discovery fresh in her mind. She was not interested in repeating the experience. For goodness' sake, she was not suicidal! Months of meticulous planning for each and every delivery was useless
in the glare of John Winchester's detective skills. It would not be long for the others to figure it out. She would be imprisoned – tortured for every remaining day of her life – and if she escaped, her life would be Castiel's. The life of a Fallen,
an outcast forever. Her eyes hardened. This was not worth risking her life again. She opened her mouth to decline, only for her decisive 'no' to die on her tongue at the sight of Mary.

Hope and desperation rolled off her in waves as she set the freshly-cooked chicken on the table, expression betraying no hint of emotion. Slowly, she drew a pair of manila envelopes from the pocket of her apron, purposefully laying them before her.

'I need to give my boys a proper goodbye,' Mary stated simply,' They've been through so much with so little and they deserve a chance to hear from their mother one last time.'

Anessa gnawed on her bottom lip, staring up at the expectant couple. In that moment, she knew. She did not have the heart to extinguish the spark in their eyes. 'I'll do it,' she relented, sealing her own fate.

She picked the letters up determinedly. These were going to reach Sam and Dean Winchester – by hook or by crook. She had made her bed – it was now time to lie in it. The smile on Mary's face was practically glowing as she wrapped her arms around her,
pressing a kiss to her hair. 'Thank you. Now, we eat.'

But they never did.

Something tore her away from them – throwing her out of Heaven's gates. The next thing she knew, she was falling.